How much do you really know about one of the biggest media stories of all time?

Ryan Holiday, the author and strategist behind the marketing expose “Trust Me, I’m Lying,” is back with a book about the famous battle between billionaire Peter Thiel and the now-defunct website Gawker.

Thiel had it in for Gawker after the site revealed in 2007 that he was gay, but the investor was smart enough to bide his time until he could catch Gawker doing something illegal: publishing without permission parts of a sex tape of Hulk Hogan and his former best friend’s wife.

In his new book, “Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue,” Holiday gives an insider’s perspective on the famous Gawker takedown based on his time with both Thiel and former Gawker chief Nick Denton.

According to Holiday, Thiel’s chance meeting with a mysterious “Mr. A” was the turning point. “Mr. A” and attorney Charles Harder worked together to find any potential dirt on Gawker and jumped on the opportunity when the site published the Hogan footage.

Where is “Mr. A” now? Holiday didn’t say who he was or exactly what he’s doing now, but it’s a safe bet to imagine he’s set for life.

“I would imagine when you solve a problem for a billionaire like this, the world is sort of your oyster from that point forward,” Holiday said.

Want more? Listen to the full interview with Holiday in Hour 2 of today’s show here:

GLENN: Do the ends justify the means? Are there real white hats and black hats anymore? Can you actually be a white taking down a black hat?

If you've done them in nefarious ways, are you wearing a gray hat, or are you wearing a black hat?

There are so many things today that we would all like to see, you know, dishonest, bad media go away and collapse on its own weight. We might even cheer when something like gawker, which was a despicable website, when gawker went out of business and had to shut down, we might all cheer.

However, are we all comfortable with the idea that a billionaire can conspire and make that happen?

Even though, the end is good.

STU: Ryan Holiday is an author. He wrote a great book called Trust Me On Lying, which is a fantastic read, to go back and see how the news you see every day gets to you.

GLENN: Sausage.

STU: It's incredible.

GLENN: You'll find teeth and shoes in it.

STU: You have to read that. The new book is Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue. And it's -- it brings us through this entire story, and Ryan joins us now.

GLENN: So, Ryan, can you tell this story like only you can? Tell this story before we get into what we're supposed to learn from it.

RYAN: Well, it's an almost unbelievable story. In 2007, Gawker Media, a gossip website in New York City, has a Silicon Valley arm called Valley Wag, and they out the Silicon Valley investor Peter Thiel as gay. He's at that point the founder of PayPal. He was an early investor in Facebook, but a relatively unknown person whose sexuality was known to his friends. But he was not publicly gay.

He's -- he's humiliated by this. He's frustrated by it. He's hurt. Gawker's headline, I believe, was Peter Thiel is Totally Gay, People. So imagine your most sensitive secret being made public in such a flippant way. And he finds this not to be illegal, but to be disgusting. And --

GLENN: Now, hang on just a second. Ryan, when this happens with gawker, is this -- because I find gawker despicable. They've done things to me and my family that are just despicable.

RYAN: Sure.

GLENN: But on this, people were saying, well, we should out people, because that's only going to make people more comfortable with -- you know, with gay people if they know you're around them all the time. So were they using the ends justify the means at that time to do something good, or are they just dirtbags?

RYAN: I think it's a little bit of both, right? I think they thought, why should he keep this secret? And I think they also thought, why should this be a jet? This isn't something to be ashamed of. But the truth is be with he didn't want it to be public. And I believe that's his prerogative.

GLENN: Yeah, it's his story to tell, not anybody else's.

RYAN: He sort of despairs of being able to do anything about it for five years. He just sort of sits on this. He's frustrated. He's hurt by it. But he can't do anything about it. And it's only in 2012, when Gawker makes another enemy, they run an illegally recorded sex tape of the professional wrestler, Hulk Hogan, that Thiel sees the opportunity that he's been looking for this whole time, that he had been looking for. He had hired a lawyer to spot opportunities like this.

He approaches Hulk Hogan, and he says, look, what they did to you is not only despicable, I think it's illegal both federally and in Florida, where you're a resident. I will fund this. Thiel approaches him through an intermediary. This is totally in secret.

I will fund this case as far as you're willing to take it. And he approaches a number of other people in similar cases. And then for the next four years, this case winds its way through the legal system. And he eventually wins 140 million-dollar bankruptcy-inducing verdict against Gawker in Florida, to the shock of all onlookers and legal strategists at the time. And he achieves that thing that he had set out to do in 2007, which was to both get his revenge and to prevent this -- this website that he believes to be evil, from doing what it did to people.

GLENN: He's a really nice guy. Doesn't seem like a guy who is driven by vengeance. But does sound like a guy -- or feels like a guy who will take all the time necessary in the world. He is not in any hurry. He'll wait until it's right.

RYAN: Well, that's what's so brilliant about what he did. I think most of us, when something is done to us, we react. We respond. Right? A fight breaks out.

A conspiracy, to me, is more something that bruise, that develops. And that's what it was so brilliant about Peter. He didn't -- he said, look, what they did to me I don't think was right. And I'm angry about it. But it's never good to be driven by anger. And so, instead, he steps back. He never forgot what happened. But he looked for an opportunity, where he actually had legal -- legal ground to stand on, where he actually could have an impact. Where the public would be so universally repulsed by what these people did, that he would have a shot at making a difference. So I think both that patience and that ability to be strategic, is why he was able to solve a problem, if that's what you want to call it. That many other powerful people had looked at, and said basically, there's nothing you can do about this.

GLENN: But he didn't do -- did he become the thing that he despised?

I don't get the impression that he did. He -- he did this on the up-and-up. The only thing -- the reason why it's a conspiracy is, he didn't want to be out front. But now that it's known -- he doesn't mind. I mean, he's owning it now.

RYAN: Sure. Look, I think secrecy is a fundamental element of a conspiracy. And I respect that he was willing to see that the optics of a billionaire being publicly in front of this thing completely changes how the public would look at it. You know, he said to me, he got this advice from one of his friends. His friends said, Peter, you have to choose your enemies carefully because you become just like them. So that's really the danger of spending nine years scheming to destroy or ruin someone or something, is that you study them so much, they consume so much of your mental bandwidth, that you can kind of become like them.

I don't think that he became anything like Gawker. But, for instance, there's a seminal moment in jury selection, where they notice that overweight female jurors are the most sympathetic to their case. Now, that's not disgusting. But there is an element of unpleasantness in selecting a juror to then exploit their most vulnerable body issue to win a case --

GLENN: But don't you think -- that's done in the court system every day of the week.

RYAN: Agreed. My point is, I think we -- we tend to be idealists about change.

GLENN: Yes. Yes.

RYAN: We think that we can make change without getting our hands dirty or without dealing with some of this unpleasantness.

GLENN: Yes.

RYAN: And so there's compromises of pursuing something of this magnitude. And I think Peter was so committed to what he was doing, that he felt that that end did justify -- that means did justify the end.

STU: Hmm.

GLENN: So Ryan has spent a lot of time with Peter Thiel. Peter Thiel -- this is not an anti-Peter Thiel book. Peter worked side by side. He had unprecedented access to Peter. And while Peter didn't -- I don't think, Ryan, unless there's another conspiracy theory. He didn't fund this book. He just gave access. More with Ryan Holiday.

The book is Conspiracy. And there's some tough questions that we have to ask ourselves. More in a minute.

GLENN: We're with Ryan Holiday, he's the author of a book called Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue. It's a very tough question that we have to tackle, but I want to get a couple more facts out of the way here before we do with Ryan.

STU: Ryan, a couple of things that we picked up from the book, one thing that Peter had conversations about his strategy, trying to get Gawker to go away.

RYAN: Uh-huh.

STU: They discussed at least seemingly -- he comes off a little flippantly, but at least considered doing things actually illegal when it comes to the approach.

GLENN: Yeah. What was the -- what was the example, Stu?

STU: Well, I'm sure -- I'm sure Ryan can walk us through the examples. I don't have them in front of me.

RYAN: Sure.

GLENN: Go ahead, Ryan.

RYAN: Sure. It struck me as a little bit of a tempest in a teapot by the media coverage. Because it's like getting in trouble for thinking about speeding and then not speeding.

GLENN: Yeah.

RYAN: But, you know, if you think about Thiel's position, he finds Gawker to be this great evil. He's trying to do something about it. But as a billionaire, he has essentially limitless resources. He's also the majority owner of one of the most powerful in intelligence and defense companies on the planet. So he has these immense resources.

And so it's a question then of, which of them is he going to use and what limitations is he going to impose on himself?

So theoretically, could he hire private detectives to follow Gawker writers and attempt to find dirt on them, that would be embarrassing? Could he start a rival website that would focus, but nothing on their personal lives? Could he bribe employees to leak information to him? Could he -- could he lobby politicians to go after them?

Like there's many things that he could do. But what he decides, actually, early on, after sort of laying all these options on the table, is that he -- that he wants only to do what's legal and ethical, because he's -- he's both, I think an ethical and moral person. But also, because at some point, your involvement is made public. At some point, you win.

And then the public looks at what you did, and they judge you for this. Right?

And so his belief was that, if they accomplished this thing they were trying to accomplish with unethical or illegal means, the victory would stand. And it would also be, as we were talking about earlier, it would be pyrrhic, in that it would come at a great cost to himself because he would have had to become the thing that he was trying to change in the first place.

GLENN: I have to tell you, this is kind of being spun as an anti-Peter Thiel book, and just that alone speaks volumes. I don't know how many billionaires there are that would have the self-control that he had, to say, no, I want to do it -- I want to do it the right way.

Can you tell me anything -- because you have an exclusive in this about a guy named Mr. A. I know you're not going to tell me who. But what is Mr. A's role?

RYAN: Well, that's -- it's one of the weirdest twits of this story, this incredibly well-covered story.

I think people thought, I guess myself included, felt like Peter Thiel was involved on a day-to-day basis. And, in fact, he sort of follows the start-up model, which is, in 2011, he has -- he has dinner with this promising young college graduate, who has told Peter he has an idea. They sit down to dinner.

And this kid says, Peter, I think I can solve your Gawker problem. I think that buried in their archive of posts are illegal acts or acts that make them vulnerable to -- to civil judgments. And I think -- he says, if you give me $10 million and three to five years of time, I think I can make something happen here. And basically, on the spot, Peter invests in this kid. And this kid is Peter's go-between, his operative who hires the attorneys, who vets the cases, who makes the decisions day-to-day. And Peter is -- is -- and the way that Peter puts $500,000 in Mark Zuckerberg's hands and he goes and makes Facebook, Mr. A goes and makes this conspiracy a reality.

STU: Wow.

GLENN: So what do you think Mr. A is going to be doing now?

RYAN: Well, I would imagine when you solve a problem for a billionaire like this, your world is sort of your oyster from that point forward. I think he's got basically limitless options now. And has one patron who is probably willing to back him on any project under any condition.

GLENN: Holy cow.

STU: Wow. What was Peter's motivation in cooperating with you, Ryan, on this book?

RYAN: Well, as I'm sure you guys have seen, in the coverage just talking to me. This is a story that has been intensely covered, but with such bias and such sort of tribal instincts on behalf of the media. Because the media sees what happens to Gawker. And they think, oh, that could happen to us. Let's circle the wagon. So there's been this incredible amount of judgment about what's happened.

And I think that's greatly impacted the coverage, right? To such a degree, that Peter has become, in many people's eyes, this sort of James Bond villain. And that's really not what he is, when you read him and you see what he did and why he did it. So I think -- I had written critically about Gawker many times. You know, myself. My emails were once hacked and leaked to Gawker. So I know what that feeling is like. So I was willing to at least be fair. You know, I told Peter, look, you're not going to get to see the book before it's printed. You're not going to have any input on it. I'm going to play it down the middle, but I think he at least believed that I would play it down the middle, rather than holding him up as the villain, if that wasn't true.

GLENN: Yeah. So, Ryan, there's -- if -- I'm just trying to think this through. If a billionaire -- let's say George Soros, who is not a friend of mine. If he decided to go after me and I was doing something -- and TheBlaze was doing something that was blatantly illegal. And I don't mean death by a million paper cuts, what a billionaire could do.

RYAN: Sure.

GLENN: I don't think I would have sympathy for Peter, if he had just been paper cut after paper cut, technicality after technicality, just keep him in court and bleed them dry.

RYAN: Right.

GLENN: I don't think this is a problem for the First Amendment, if they're going after things that are really, truly illegal and they're big.

And I'd like to get your response on that when we come back. What does this mean for the First Amendment? That a billionaire can mark somebody and then take them out? Is that good for the republic? When we come back.

GLENN: I am -- I'm currently on a -- on a couple-week rant of, we've got to do something, and how that always leads to bad things. You just don't make good decisions when you're angry, upset, emotionally. We've got to do something usually also means, I'll violate my principles because I want this pain to stop.

So what are our principles? I -- I don't -- I didn't like Gawker. Gawker did some things that were dangerous for my family. I thought they were despicable people. And I did wish them to go out of business. But I wouldn't have done anything to get them to go out of business. And I like the way Peter Thiel did this. He waited to see, is there something that they have done that breaks the law? When they had Hulk Hogan, that was an illegally recorded tape. And for what? What was the purpose of exposing that?

So Peter took them to court on that. The problem is, he's a billionaire, has unlimited resources. And are we setting a precedent that somebody who has an axe to grind can put another company out of business? One man can put a media company out of business if they want to?

Are we -- did anybody learn that lesson in a negative way? Ryan is with us.

Ryan Holiday is the author of the book Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue.

What have you come to, Ryan, on that?

RYAN: Well, that is the big question. And it is potentially scary to think a billionaire could shut a media outlet down? And then when you step back, you know, your point about not reacting emotionally, well, did Peter actually do anything new that doesn't happen every day, anyway, right? The ACLU. The Sierra club. The NRA. They back cases all the time that they think move their ideology forward or stands up for one of their constituents. And so the idea of a wealthy person backing a lawsuit, not out of financial gain, but out of ideological alignment is actually not remotely new. And if you were to ban it, society would undoubtedly become a worse place, right?

Why shouldn't your rich uncle be able to support you against a person who ran into you, with their truck, right? You want that.

GLENN: So there's the legal question, which I think he did everything right. And then there's the ethical question, which I think he did everything right.

But you have to ask that ethical question too. And would you have felt different if he would have taken Gawker on, with -- with almost frivolous lawsuits and just done death by 1,000 paper cuts? Do you think it would have been a different story for you?

RYAN: Absolutely. Because there you're not attempting to win. You're not attempting to have your argument validated. You're attempting to destroy someone for something they may not have done something wrong.

So Peter's decision, for instance, not even an attack on First Amendment grounds because he believes that's sacred. But to look instead at the individual's right to privacy, right? Is there a newsworthiness in this sex tape, or is there a copyright claim here? He specifically did not sue them on say frivolous, libel, or defamation grounds because he was worried about the precedent that it might set. And he didn't believe that there was anything wrong there.

So his distinction is really, really important. And I think, you know, a potential hypothetical would be, what if a liberal had backed Shirley Sherrod in her lawsuit against Breitbart, when they ran that deliberately edited, manipulative tape of her in I believe it was 2011.

GLENN: Yes.

RYAN: And I don't think many of the people who are deeply upset about what happened to Gawker, I don't think they would be upset if Breitbart had gone out of business in 2012. I think they would be cheering at the exact same way.

STU: It's very interesting. Yes, that's absolutely true. I wanted to get your take quickly on -- I can't remember the guy's name who actually wrote the story.

But he -- he's become somewhat of a cause celeb on the left of a guy -- because he's not the guy -- he's not Nick Denton who ran Gawker. But the guy who actually just did the post.

He's a lowly --

Yes. Yes. Just -- you know, a writer. And he's working for Gawker. Not making a ton of money. And he was involved in this lawsuit. And he has been presented as this guy who got in the middle of this thing. And he was helpless in this situation. And now he has no chance of making any money. He owes an ungodly amount of money for this lawsuit and can't do anything about it. He wasn't wealthy. He didn't own Gawker. Do you have any perspective on that and how that went down?

RYAN: Yeah. So in a way, he's just doing his job. Gawker publishes these stories all the time. It's so unremarkable when you get to the Hulk Hogan tape, that Nick Denton, the CEO isn't even notified, right? The case that bankrupts the company, the CEO doesn't know about it until after it is published. Because that's how run-of-the-mill it actually was.

So, yes, it was unfortunate that this individual, this writer doing his job, takes the full brunt of it in the public eye. You know, during the trial. And then is held liable -- the jury says -- holds him personally liable for about $100,000 of this 140 million-dollar judgment. But what people forget is that months after the verdict, Peter and Hulk Hogan settle with Gawker that releases both Denton and Daulerio from these individual claims. And they're able to walk free.

You know, they were not necessarily ruined by it. And Peter said, look, my goal was to destroy Gawker, not to ruin these people personally. But individuals are held accountable for their actions.

GLENN: Yeah.

RYAN: And that's life.

GLENN: I mean, we all have choices, no matter if everybody else is doing it. We still have a choice.

You know, I'm so intrigued by Peter. I think he is a real force for good. And I think he's a deep and thoughtful man, that doesn't make everything that he -- everything that he does right or good. But he really seems to think about things.

RYAN: Yes.

GLENN: And I heard him say once, it's not that I think I'm right, I'm not even sure if I'm right, I just don't think other people are even thinking about these things. What does that tell you about him?

RYAN: He would say that even about this case. That it's often not that he was right and other people were wrong. It's that Gawker wasn't even -- Gawker just assumed that this Hulk Hogan case would get settled. They weren't even taking it seriously. And so Peter is a person who has theories about the world. And he's willing to put some skin in the game. Right? He's willing to throw some weight behind them and see what happens. And I think -- to me, the lesson of what happened, and what I tried to write about in the book, is that, you can fundamentally disagree with what Peter did, and you can think that it's dangerous and alarming that Gawker doesn't exist anymore. But there is something to study, a lesson to learn, about how this guy did it. And why he did it.

And how he was able to effectuate the change that he needed to happen, outside of writing op-eds or putting out a petition. You know, he -- he made real change in the real world, where other people said, there was nothing you could do about it. And to me, that's a lesson that -- and in some ways, that's an inspiring things right now, in this society, where we're stuck, you know, on both sides of the aisle. I think we just feel like change can't happen. And here, a guy made something happen.

GLENN: Yeah. When -- I saw that in the book that -- that phrase.

I -- I thought to myself, that is something that the world is not even rewarding now. It doesn't reward you to think. It doesn't reward you to think outside of the box and to think differently. And it doesn't reward you to say, I'm not sure if I'm right. I just want us to think about that. And that's really what we're missing.

RYAN: And the irony is that in some ways, Gawker was part of that problem, right? I think one of Thiel's objections to them is not just the despicable things that they did and the violations of privacy, but as the site that just sort of made fun of everyone for every mistake, every failure, every personal idiosyncrasy.

They were dis-incentivizing people from thinking outside the box, from being weird. And weirdness is where innovation comes from and creativity. And we should want people to take risks and turn out to be wrong. What we don't want to do is mercilessly mock them, to the point where nobody tries anything because they don't want to end up on the front page of Gawker.com or any website.

GLENN: Ryan Holiday, thank you very much.

RYAN: Thanks for having me.

(music)

STU: I think we sold you on that story.

GLENN: Good story.

STU: Ryan tells it well.

GLENN: Good book.

STU: And there's a lot in here that's not previously been reported on.

Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue by Ryan Holiday. Also, we should have Ryan back on for Trust Me On Lying.

GLENN: For Trust Me. Yeah. He is a guy who has had firsthand experience, really, with fake news. I mean, it was really kind of his job as a PR person.

STU: Yeah.

GLENN: And he knows how it works. And it's really fascinating.

STU: Yeah. Quickly on it, the concept in that book was that he -- you know those weird stories that bubble up to the national media. And you're like, how did we even hear about that?

It was his job to try to get them elevated from -- from a blog to a local media, to regional media, to national media, to try to get attention for clients and all sorts of stuff. So he was in the media manipulation business for a long time.

GLENN: And, you know what, it goes to -- remember the first thing that I said when we went to CNN and I said, I'm really uncomfortable with this. The ingesting of news.

STU: Oh, yeah.

GLENN: Because if you make one mistake, that is your basis forever.

STU: Uh-huh.

GLENN: And it's interesting. Because what he did was, it was on a blog. And then he would call the local news and say, did you see this? Did you see this blog?

STU: Did you see this blog?

GLENN: And they would use that as a credible source. And then he'd go to the regional news and said, did you see this in the newspaper? And it got more incredible as it went on.

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